20 days in Chicago, Washington DC & New York City Itinerary

20 days in Chicago, Washington DC & New York City Itinerary

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Route & dates

20 days in Chicago, Washington DC & New York City Itinerary

Start: Ulaanbaatar
Fly:  23​h 15​min
1
Chicago
— 3 nights
Fly:  3​h 45​min
2
Washington DC
— 7 nights
Fly:  3​h 15​min
3
New York City
— 7 nights
Fly:  17​h 45​min
End: Ulaanbaatar

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Do your shopping at The Magnificent Mile and L. H. Selman Ltd. Step out of the city life by going to Cowles Bog and Oak Savannah Trail. Explore Chicago's surroundings by going to Whiskey Acres Distilling Co. (in DeKalb) and Illinois Holocaust Museum & Education Center (in Skokie). Next up on the itinerary: explore the world behind art at The Art Institute of Chicago, contemplate in the serene atmosphere at Fourth Presbyterian Church, engage your brain at Museum of Science and Industry, and see the interesting displays at Swedish American Museum.

For maps, traveler tips, photos, and more tourist information, refer to the Chicago driving holiday planner .

Ulaanbaatar, Mongolia to Chicago is an approximately 23.5-hour flight. The time zone difference when traveling from Ulaanbaatar to Chicago is minus 14 hours. Prepare for a bit warmer weather when traveling from Ulaanbaatar in June: high temperatures in Chicago hover around 32°C and lows are around 20°C. Finish your sightseeing early on the 21st (Fri) so you can travel to Washington DC.

Things to do in Chicago

Museums Shopping Parks

Side Trips

Illinois Holocaust Museum & Education Center, Whiskey Acres Distilling Co., Oak Savannah Trail, Cowles Bog
Highlights from your plan
Whiskey Acres Distilling Co. ©
Whiskey Acres Distilling Co.
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum

7
nights
Washington DC

Washington DC ©
The capital of the United States, the District of Columbia contains the lion's share of the country's most treasured monuments, memorials, and public museums.
Antietam National Battlefield and Gettysburg National Military Park will appeal to history buffs. Step out of the city life by going to Old Rag Mountain Hike and Mount Vernon Trail. Venture out of the city with trips to Gettysburg (Devils Den & Gettysburg National Cemetery) and Limberlost Trail (in Shenandoah National Park). There's much more to do: examine the collection at National Air and Space Museum, contemplate the waterfront views at Tidal Basin, admire the masterpieces at National Gallery of Art, and take in the spiritual surroundings of Washington National Cathedral.

To find other places to visit, traveler tips, reviews, and other tourist information, go to the Washington DC trip itinerary builder website .

You can fly from Chicago to Washington DC in 4 hours. Other options are to do a combination of flight and train; or drive. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Washington DC. Traveling from Chicago in June, plan for a bit warmer nights in Washington DC, with lows around 24°C. Finish your sightseeing early on the 28th (Fri) to allow enough time to travel to New York City.

Things to do in Washington DC

Parks Museums Historic Sites

Side Trips

Gettysburg, Shenandoah National Park, Mount Vernon Trail, Antietam National Battlefield
Highlights from your plan
Antietam National Battlefield ©
Antietam National Battlefield
National Air and Space Museum ©
National Air and Space Museum
National Gallery of Art ©
National Gallery of Art

7
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Shop till you drop at Fifth Avenue and Yunhong Chopsticks. Get in touch with nature at East River Waterfront Esplanade and Hamilton Grange National Memorial. There's still lots to do: admire the masterpieces at The Metropolitan Museum of Art, race across the water with a speed boat tour, go for a walk through Central Park, and take in panoramic vistas at Empire State Building.

To see more things to do, reviews, and tourist information, go to the New York City trip itinerary planner.

Getting from Washington DC to New York City by flight takes about 3.5 hours. Other options: take a train; or drive. While traveling from Washington DC, expect little chillier days and about the same nights in New York City, ranging from highs of 31°C to lows of 21°C. Wrap up your sightseeing on the 5th (Fri) to allow time to travel back home.

Things to do in New York City

Museums Historic Sites Parks
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
American Museum of Natural History ©
American Museum of Natural History

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